


Flirting 101

by theferociousbeast



Category: Supernatural
Genre: Alcohol, Alternate Universe - Human, Anal Sex, Bisexual Dean, Blow Jobs, Bottom Dean, Jo Harvelle & Dean Winchester Friendship, M/M, POV Third Person Omniscient, Past Tense, Pick-Up Lines, Porn With Plot, Top Castiel, Virgin Castiel
Language: English
Status: Completed
Published: 2015-04-04
Updated: 2015-04-04
Packaged: 2018-03-21 04:39:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,065
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3677829
Author URL: https://archiveofourown.org/users/theferociousbeast/pseuds/theferociousbeast
Summary: <blockquote class="userstuff">
              <p>Castiel doesn't have much dating experience. Any, really, unless you count the time he made out with Meg Masters. But Gabriel is set on changing his brother's fate, or rather, imminent death at the hand of felines. As much as Castiel dislikes being forced to read relationship advice books, maybe a night out at The Roadhouse isn't such a bad idea.</p>
            </blockquote>





	Flirting 101

**Author's Note:**

> Hey, y'all! I got the idea for this ficlet from a shopping trip to the Goodwill, and my darling Emily who decided Cas needed to read the god awful books I found. The books mentioned are, in fact, real, should you, too, decide you need help with the ladies. I hope it ends as well for you as it does for Castiel.

Castiel didn't have much dating experience. Any, really. Seeing as his people skills as a whole were “rusty,” dating was out of the question. Besides, the opportunity never arose.

He thought he had been particularly smooth with Meg Masters, having learned from one particular adult film starring a pizza man and a babysitter. But whatever their relationship could have been considered, it didn't last much longer than a steamy makeout session.

Gabriel had had enough of his baby brother sitting around at home all day, surrounded by books and cats. So he made Castiel an offer he couldn't refuse: a trip to the bookstore...to buy more books?

“You don't know anything about the ladies, Cas,” Gabriel complained on the way to the bookstore. The car they were driving was one example of this blatant lack of knowledge: Castiel's car was something between gold and “grandma tan,” a car from the 70s that Gabe referred to as the Pimpmobile.

“I have found that women are quite similar to felines, Gabriel,” Cas replied. “Their interests include eating, and being affectionate on their own terms. When a line is crossed, they will not hesitate to bite or scratch.”

Gabriel could only roll his eyes and sigh. Meg Masters had not exactly been “your average girl,” and Castiel using her as a comparison to every other woman wasn't exactly healthy.

“Yeah, well, we'll see about that.” The Pimpmobile rolled up to the curb in front of Fitzgerald's New & Used Books, and for a moment, Castiel seemed hesitant to get out of the car. Gabriel briefly worried that he would have to take his brother to the mental hospital instead. Since when did Cas have an aversion to bookstores?

Reluctantly, however, he pushed the door open and stepped out, making his way to the store's entrance. Gabriel let out a sigh of relief. _Step one, done._ A bell tinkled overhead as the heavy door was pushed open, and Castiel was met with the comforting scent of old books, a too-happy man at the cash register, and a fluffy cat weaving between his legs. This was his heaven.

Not five minutes later, as he browsed the section of books labeled Religion, Gabriel shoved a pile into his arms. He tilted his head to the side quizzically, eyes narrowed as he looked to his brother. Gabriel beamed, explaining that, “these are for you, baby bro. Maybe they'll teach you a thing or two.” As he walked away, Castiel examined the books in his arms. Flirting 101 and How To Succeed With Women. This was going to be a long day.

* * *

 

It had taken Castiel two days to finish reading the books Gabriel insisted he buy. He didn't have much choice, really. Gabriel had locked him in the hall closet with nothing but a light and the books, insuring that he wouldn't choose an alternative reading material.

He felt a bit like Harry Potter, but without the magic. Things would have been so much easier if he could have unleashed a giant snake to attack Gabriel.

At the end of the second day, Gabe let him out on the condition that he go one one more adventure. Castiel was desperate enough to get out that he even consented to Gabriel's pleas to pick out his outfit, too.

When Castiel stepped out of the Pimpmobile this time, he sported a gray, long-sleeved henley, the buttons undone against his sternum; tight, black jeans; and a pair of classic Chuck Taylors.

Even Gabe couldn't help but let out a low whistle as his brother rounded the car. The Novak family had some damn good genes, and Castiel averting attention from those bright baby blues, cheekbones you could crack open a cold one on, and ridiculous sex hair through the use of a trenchcoat and business casual attire was a travesty.

The door they opened this time was not to a bookstore, but to The Roadhouse, a bar out in the middle of literally nowhere that was frequented by...truckers, Castiel had to guess. He had no clue why his brother thought this would be a good place to pick up girls, but the burgers were excellent.

The first girl he worked his charm on was the bartender, a blonde girl in her early twenties with a sweet smile and a dirty mouth. His opening line, an honest compliment of “you are extremely pretty,” wasn't so bad, and Gabriel had to stop himself from pumping his fists as he sat at a booth.

But the line that followed was a little less than skilled: “May I buy you a drink?”

The girl cocked an eyebrow, an amused grin spreading across her face. She took a glance to either side of her, observing the bar she worked at, before replying. “Dontcha think I could take care of that myself, lover boy? Try asking someone who doesn't work here.”

She was of good humor, however, and offered Castiel a drink instead. She introduced herself as Jo Harvelle, the daughter of The Roadhouse's owners. “You're lucky you've got that puppy dog face, Casanova. I'm know to punch guys for getting drunk and frisky with me, just ask Deano over there,” she warned, shooting a smile down the bar to a guy sitting by himself, a tumbler of whiskey resting on the counter before him.

The guy perked up at hearing his name, and smiled slyly at Jo. He hadn't noticed Castiel yet, but Castiel had noticed him. He wore a plain black t-shirt under a green flannel, a pair of tight faded jeans, and dusty brown boots. His green eyes sparkled in the overhead lighting of the bar, freckles dusted all over his face, and his tongue briefly jutted out to lick an unseen droplet of whiskey from a plush pink pout.

“You call me, Joanna?” He called, and if Cas was distracted by his appearance, damn him to all hell if he didn't almost fall off of his barstool after hearing that voice. It was gruff, like gravel and three packs a day, but fell on the ears with a bold sweetness like dark chocolate or Jim Beam bourbon.

“My buddy Cas 'ere doesn't know about my reputation, Deano. Tell him what I do when the guys have one too many and think they can make a move on me,” Jo replied, the smug smirk never leaving her face. Castiel could sense that she was being friendly, but the words still threatened to trigger his fight-or-flight response.

Dean looked at Castiel, then, and his eyes lit up with something coy and animalistic. “Jo's got a mean right hook, Cas. She looks like a little shrimp, but she'll kill a man if she's gotta,” he warned, his smirk mirroring Jo's own as they both looked to Castiel.

“Aw, Dean!” Jo cried, walking over to pull the man into a headlock, rubbing her knuckles roughly into the top of his head. Castiel noted that this was what Gabriel referred to as a noogie.

Then, Dean laughed. And it was such a glorious sound that Cas couldn't help but stare, lips parted in awe. He questioned, then, whether the meaning of life was really 42, or if Douglas Adams had simply never heard Dean Winchester laugh. It was a long laugh, lasting much longer than the noogie itself, and with the way he threw his head back, Jo was lucky he didn't knock her out.

When the laughter died down, and Castiel had expectant eyes watching him, he barely managed to utter out a quiet, “Gabriel told me I had to practice...wooing the ladies.” His voice carried such a tone of defeat, that after a few seconds of silence, Dean and Jo both busted out with laughter.

“Cas, you are looking at the master of seduction,” Dean exclaimed, grinning. Castiel, befuddled, furrowed his brows as he replied, “Jo is interested in women?” His words were dripping sincerity, but all he felt as the two erupted into yet another round of hysterics was frustration.

Dean could sense this, it seemed, and so he pushed down his laughter and clapped a hand down onto Castiel's shoulder. “No, Cas, Joanna likes dudes. _I'm_ the master of seduction.” His face had softened into an expression kinder than Castiel had seen it all night, his voice quieting a level or five. There was something about it that made Castiel feel as if it was just the two of them now, and the words Dean spoke were meant for no one but him.

“Oh...” came Cas' reply, slow, as if he was still registering Dean's words. “Dean, would you mind teaching me how to talk to women?”

* * *

 

And that's how Castiel found himself sitting next to Dean Winchester, being taught the basics of human interaction. Gabriel had left long ago with a woman named Kali, a waitress at the Roadhouse who he'd picked up at the end of her shift.

“Never use pick up lines like, 'did it hurt when you fell from Heaven?'” Dean suggested, putting up a finger to call for a round of shots. Castiel nodded slowly, brows furrowed as he took in the information Dean was giving him. “Girls hear that shit all the time. They know it's coming before you even open your mouth, swear to God,” he added, downing a shot out of his trio – The Three Wise Men, he called it, or Jack Daniels, Johnny Walker, and Jim Beam.

“Ryan Gosling plays this real charmer in Crazy, Stupid, Love. 'S a chick flick, Cas, don't watch it. But what he does, he goes up to these chicks at the bar, and the guy is classy as all hell, you know? You just look at him and hopes he takes you home. So he get's the girl's name, and all he does is ask, 'wanna get out of here?'” He continued. Castiel heard him, but all he could look at was the way Dean's forefinger traced the rim of his empty shot glass.

“I've never tried that line, it's real bold. But you've got the right kinda look to pull it off, Cas.” Castiel could have sworn he saw a blush creeping up Dean's cheeks as he said this, but he downed another shot before it could be addressed.

“Here. I'm gonna go sit down there, act like we haven't met. Why don't you try it out? Pretend I'm a hot chick or something,” Dean suggested, fluttering his eyelashes and puckering his lips before breaking out into laughter.

“Yes, we could try that,” Cas replied, smiling faintly at how ridiculous Dean's face was. Dean nodded in affirmation before claiming a seat in a corner of the Roadhouse. Cas waited a minute, then, taking deep breaths and downing Dean's remaining shot before walking over.

“Excuse me,” he spoke up, coming into the other man's line of vision. When Dean looked up, feigning surprise, Castiel smiled slyly. “I don't recall seeing you around here before. I'm Castiel,” he said, and the words came out so low and smooth like velvet that even he was surprised.

“I'm, uh...I'm Dean. Dean Winchester,” Dean replied, the look on his face now one of genuine surprise, those plump lips of his parting slightly in his stupor.

“You wanna get out of here, Dean?” Castiel asked, holding out his hand not for Dean to shake, but to take and run away with. Dean looked at it tentatively before nodding, taking it within his own.

“Yeah, Cas. I do.”

Castiel beamed at this, pulling a tenner out of his pocket to put down on the bar before leading Dean out of the Roadhouse. Jo could keep the change. Goodness knows she deserved it for getting him into this mess.

“This is my Baby here,” Dean said as they approached a shiny black '67 Impala. The proud smiled on his face mirrored Castiel's thought that he took extremely good care of her. Cas climbed into the passenger seat, Dean in the driver's, and Castiel fancied that it almost smelled as nice as old books. It was leather, motor oil, and something warm and earthy that he imagined must have been Dean's own scent. He inhaled deeply, relaxing into the smooth leather seat.

As the engine roared to life, AC/DC began to stream through the speakers, and Cas melted at the way Dean hummed and strummed his fingers against the steering wheel as he pulled away from the Roadhouse and towards his own home.

When Bon Jovi's 'Livin' On A Prayer' came on, both men simultaneously found it appropriate to sing along at the top of their lungs. “ _We gotta hold on to what we've got, it doesn't make a difference if we make it or not. We've got each other, and that's a lot. For love, we'll give it a shot._ ”

“Bon Jovi rocks, on occasion,” Cas said, smiling over at Dean. Dean turned his head to meet the gaze, his face showing every sign of struggle between excitement and shock before quickly averting his gaze back to the road ahead of them.

“Y'know, Cas, you're making it really hard for me to not just pull over right here and screw you in the backseat,” Dean muttered, death grip on the steering wheel turning his knuckles white. Cas could second handedly feel Dean exerting more pressure on the gas pedal, and he smiled out the window.

“What have I done to lead you to believe that I am a bottom, Dean?” He questioned softly, grinning when Dean struggled to keep himself from swerving off the road.

“Jesus Christ, Cas. I don't care what the hell you are, but I'm giving you ten minutes from the time we step through my door for you to get your dick in my ass.”

It couldn't have taken any longer for them to make it home. Dean was getting more antsy by the minute, so Castiel took it upon himself to rub the man's hardening length through his tight denim jeans until the Impala was safely parked in Dean's garage.

“ _Out,_ ” Dean demanded, hurriedly getting out of the car and locking up as Cas followed suit. He fumbled with the keys to his house, picking out the wrong one several times and almost giving up and letting Cas fuck him in the garage instead. Finally he got the door open, and Castiel barely had time to step inside and close it behind him before Dean had him pressed against it, all hungry lips and wandering hands as they kissed.

Cas let out a wrecked, virginal moan as he felt Dean's denim clad hard on rut up against his own, and could only let another escape when Dean asked, “you like that, Cas?” and ground his hips against him again.

Castiel hurried to rid Dean of his flannel overshirt, pushing it over his shoulders and pulling it down his arms without letting their lips part. “Shirt off,” he demanded, pushing the other man back a step to pull the black t-shirt over his head. At this distance, Cas was given the opportunity to look at Dean, a wild, spit-slick smirk gracing his face and a deep blush making its way from his cheeks to his chest, which rose and fell heavily with each gasp for air.

“You, too,” Dean said, stepping closer to toy with the hem of Castiel's henley. His teasing movements lacked the urgency of Cas', thumbs dragging across the warm flesh of Cas' abdomen as he slowly raised the shirt up and over his head. When it had finally joined the pile of Dean's shirts, Castiel rejoined his lips with Dean's, settling into his slower pace as he undid the button and fly of Dean's jeans.

Dean toed off his boots as Castiel worked on dragging the denim down his thighs, planting soft kisses against his stomach, hips, thighs, knees. He took a detour to nuzzle against Dean's length through the fabric of his boxer briefs, earning a quiet whimper from him. Once Dean had stepped out of his jeans, he got to work on Cas', repeating the process to leave the two men in their underwear and a heap of clothing on the living room floor.

Dean led Castiel up the stairs, then, taking breaks every few steps to press his body against the other man's and kiss him, fingers entangling themselves through a mass of dark hair. Castiel finally settled on lifting him up, letting him wraps his legs around his waist and his arms around his neck, still kissing as he tried to navigate to Dean's bedroom.

“To the left, end of the hall,” Dean mumbled against his lips before sneaking his tongue back into Castiel's mouth, licking up the taste of Tennessee whiskey. As Castiel turned the doorknob, Dean's weight shifted, brushing his ass against Cas' hardened length, resulting in a chorus of moans from the both of them.

“Fuck, Cas, come on,” Dean pleaded, tightening his grip around him. Soon enough, his back was meeting the fabric of his comforter, and he felt Cas' knees coming up to straddle his hips.

“Are you sure this is okay, Dean?” Castiel asked between planting kisses along Dean's jaw and down his neck, sucking a bruise into the hollow where his neck met his collarbone.

Dean let out an obscene moan, threading his fingers through Cas' hair once more, bucking his hips up to meet the other man. “Yeah, Cas. Fuck, yeah I'm sure,” he replied, nails scraping lightly at Castiel's scalp. Cas hummed happily in response, rutting up against Dean's cock as he licked at his jugular, trying to find his sensitive spot.

“Good,” was all he said as Dean moaned, before sliding his body down Dean's to lap at hardened nipples, flicking his tongue against the pink buds. He wanted Dean squirming with need before they got down to business.

He moved lower, pressing his nose into light brown curls of hair below Dean's belly button as he mouthed at the man's clothed cock, before slipping two fingers under the waistband of his boxer briefs to pull them down. Dean's cock bounded back against his stomach, leaving a trail of precum, which Castiel happily licked clean before turning his attention to the head of Dean's swollen member.

He licked up the precum beading at the slit, tracing wet circles around the head with his tongue before trailing down the length, his left hand against Dean's hip and the other toying with his balls as he moved back up to suck the whole of Dean's cock into his mouth, learning the heady flavor of the flesh like a lollipop.

“Cas, I-- swear to God, Cas, if you don't fuck me now I will come all over that pretty fucking mouth of yours,” Dean mumbled, earning a feeble attempt at a shit eating grin from Cas, who hummed against the length in reply, only continuing to suck him down. It didn't sound like such a bad idea to him, but Dean apparently thought otherwise.

“Cas, please. You gotta-- I need you to do it, Cas,” he pleaded, voice absolutely wrecked as his hips stuttered against Castiel's palms. He gave in, pulling off of Dean's cock with a pop. Dean scrambled to pull a bottle of lube and a condom out of his bedside table then, tossing them to Cas. Castiel popped the cap open, squeezing lube onto his fingers, rubbing them against each other as he nudged Dean's legs apart, reaching a slick finger down to circle Dean's hole.

He let out a whimper, lowering his hips to push down against Castiel's finger, silently begging to have the man inside him. Castiel smiled softly, pressing a kiss to Dean's hipbone as he pushed the first finger into him.

Dean let out a sound that sounded something like a sharp inhale and a moan, but Castiel stopped before pushing in all the way to allow Dean time to adjust. When he nodded, he pushed the first finger the rest of the way in, slowly massaging Dean's inner walls, coating them with lubricant.

“Another,” Dean muttered, wiggling against Cas' finger. Castiel smiled in understanding, slowly pushing a second lube-slicked digit into Dean's hole. He adjusted more quickly to this one, giving Castiel permission to scissor them inside of him; then he asked for a third, and though the stretch of muscle made him wince, the brush of Castiel's fingers against his prostate made him moan with pleasure instead of pain.

“Oh, God, Cas. Right there,” he groaned, eyes shut tight as he fisted one hand in Cas' hair and the other in the sheets. Castiel consented, slowly pulling his fingers out before thrusting them back against the bundle of nerves. “Mmm, Cas. Fuck, that's good,” Dean moaned again, not 100% aware of the words coming out of his mouth as he thrust his own hips down to meet Cas' fingers. “Fuck me, Cas. Want you in me.”

Castiel couldn't have been happier to oblige. He pulled his fingers out, earning a whimper from Dean at the loss of contact, but quickly sheathed his own hard cock before coating it in a layer of lubricant. “It's not too late to back out, Dean. I'm not going to do anything you don't want me to do,” he reminded, reaching his clean hand to card through Dean's military-short hair reassuringly.

“I really don't give a shit, Cas. You could end up being a serial killer and I'd still want you screwing me right now,” he replied, lopsided grin spreading across his face. “Now fuck me before I change my mind.” Then Castiel was slowly pushing into Dean, the thickness of his cock nothing Dean could have been entirely prepared for. The dude was friggin _huge_. He let out a filthy moan at the way Cas was filling him, and he hadn't even bottomed out yet. “Oh Cas, fuck. Fuck, you're-- so big, Cas,” he groaned, feeling more precum leak from his slit. “More, I need more,” he pleaded, begging Cas to push in up to the hilt.

Castiel leaned over to meet Dean's lips in a sweet kiss before pushing in completely, Dean groaning into Castiel's mouth. He began to move as he felt Dean's muscles relax, picking up a slow pace, thrusting in and pulling out at an angle, trying to find his prostate.

It didn't take long for Castiel to thrust up against it, and Dean reacted by telling him to move faster, increasing the rate of thrusts against his prostate. They were moaning together, now, Cas panting hot breaths against Dean's neck as he pounded into Dean, the warm walls and clench of muscles around him causing warmth to pool in the pit of his stomach.

“A-ah, Dean,” he mumbled against the man's neck, his speech cracking. “Feels so good, Dean. I'm-- close, so close.” Dean was, too, he could tell, because his hips stuttered and his nails clawed fervently at Castiel's back, moans becoming louder and more frequent as Castiel thrust into his prostate with increasing force.

He took Dean's cock into his hand, then, and pumped it in time with his thrusts, and Dean was coming before he had time to form a coherent sentence. As his muscles clenched around Castiel's cock and he repeatedly cried out the man's name, Castiel followed suit, chasing his orgasm. “Dean, oh my—DeanDeanDean,” he spluttered, his vision whiting out and his arms going weak at either side of Dean's body. He all but collapsed after riding out his orgasm, pulling out and curling into Dean's side.

“I'm... I'm not a cuddler, Cas, I--” Dean began, thinking back to other occasions when all he had to do was leave the girl in the motel room with a wad of cash and a, “thanks, sugar.” There were no awkward mornings, wondering if he had to cook breakfast, or uncomfortable nights cuddling with someone he had no intention of sticking with. But as Cas looked up at him with that goddamned puppy dog face and those bright, hopeful eyes and those lips that sang along to Bon Jovi, Dean found himself changing his mind.

“I guess it's never too late to change, huh, baby?” He asked, wrapping an arm around Castiel. Dean fell asleep cuddling that night, but whether he made pancakes and bacon the next morning is none of your friggin beeswax.

**Author's Note:**

> Thank you for reading, and I hope you enjoyed it. As always, comments and kudos are very much appreciated.


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